Across the cover and down the spine of The Love Affairs of Nathaniel P., young Brooklyn women “bursting with vibrant, almost aggressive good health” are profiled in silhouette, their pixie cuts and power bangs offering a taxonomy of the species, like butterflies pinned under glass. These are the conquests of Nate Piven, our antihero. Nate’s romantic history sounds like a lost verse of “Mambo No. 5”: a little bit of Hannah, Elisa, Juliet, Kristen, Justine, Kelly, Jean, Beth, Cara, Emily, another Emily, and a third Emily. With his frumpy Harvard intellectualism and his overblown self-regard, Nate has collected so many aggrieved ex-girlfriends that they could file a class action lawsuit. But they’ll have to settle for this book.

Adelle Waldman’s debut novel raises a wickedly fun question. Can a woman of Nate Piven’s demographic—Waldman is a young Brooklyn journalist with a book deal, just like Nate and all the sad young literary men he stands for—summon the empathy, imagination, and vocabulary required to turn the hipster Lothario of Fort Greene into a decent, relatable human being? The genius of Waldman’s question is that she wins either way. If Nate turns out to be redeemable, then Waldman will have proved that she is a masterful writer, capable of humanizing the devil himself. If he is unredeemable, then Waldman gets to flay him for her readers’ enjoyment.

Already a slim novel, The Love Affairs of Nathaniel P. can be split into three parts. In the first part Waldman delivers the most accurate, vicious, and hilarious caricature of the contemporary Brooklyn social scene to date. Overeducated, underemployed writers wander through cramped house parties and boozy book parties, saying things like “Conscience is the ultimate luxury” and “Doesn’t James Wood, like, love that book?” Nate is crafted to represent his generation. A particular species of douche bag, he is “bound by twenty-first-century chivalry” to espouse progressive politics while silently rationalizing the harm he does to people around him. While his friends and lovers banter like boxers, landing solid points about complex issues and dripping with ambition and style, Waldman dances across the line between drama and slapstick. Here’s Nate trying to avoid a lusty ex-girlfriend at a party.

His glass was empty again. The open wine bottle was on the far side of a vast, primitive-looking wooden salad bowl. He pivoted to reach for it, and as he turned, his torso momentarily blocked out everyone but him and Elisa. She met his eye and gave him one of her sultry looks, tilting her face bashfully downward and smiling a little lopsided smile that was particularly suggestive, the shy but flirtatious look a woman might wear when she confessed to some slightly offbeat sexual fantasy.

Nate’s body tensed. He became panicky and hyperalert. He felt, he imagined, like a soldier who had been having a rollicking time on guard duty until he heard the crackle of approaching gunfire. Previous reports of improving conditions had proved false. Situation on the front was actually bad, very bad.

The wine made glugging sounds as it hurried out of the bottle and splashed against the fishbowl contours of his glass.

Through the middle of the novel, Nate hooks up with Hannah, the first woman he’s ever been attracted to out of mutual respect, and they begin to date. Hannah is refreshingly real and sane, smart without being “smart.” Five months go by in third person narration, like the pages of a calendar falling off, as Waldman focuses tightly on the psychodrama of modern romance, the joys and insults hidden in simple gestures. Nate sours on the relationship, unsure of how to behave with someone he actually cares about, unaccustomed to the effort that everyday love requires. The novel takes a surprising turn at the end, and Waldman rephrases her initial question—it’s not whether Nate is redeemable, but whether romantic courtship is even possible anymore.

Until recently I lived in Brooklyn, wrote for magazines, dated, played a weekly soccer game in Prospect Park, and spent too much time fussing over my hair. So it was easy, while reading this novel, to mistake myself for Nate Piven. I tried to remember if I’d seen anyone who looked like Adelle Waldman sitting at my local pub, listening in and taking notes. The thought flattered me. It would be like Edith Wharton taking an interest in your pals. Clearly Waldman has studied her 19th century classics. The epigraph is from George Eliot, but it sounds like the finger of God pointing down from the clouds to accuse all of Williamsburg: “To give a true account of what passes within us, something else is necessary besides sincerity.” Like Wharton and Eliot and Jane Austen and Henry James, Waldman juggles with two sets of balls—incisive details about a certain slice of high society, and the kind of deeper observations about human nature that make a story timeless.

Above all The Love Affairs of Nathaniel P. offers a stirring defense of dating as a subject for serious contemporary fiction. The casual reader may wonder whether this is a chick novel about Brooklyn intellectuals, or an intellectual novel about Brooklyn chicks. Waldman rejects that kind of thinking. One of her strongest characters, a happily belligerent intellectual named Aurit, upbraids Nate for being so glib about his romantic life. “I just hate the way so many men treat ‘dating’ as if it’s a frivolous subject. It’s boneheaded. […] Dating is probably the most fraught human interaction there is. You’re sizing people up to see if they’re worth your time and attention, and they’re doing the same to you.” Another of Nate’s conquests defines dating in terms he should be able to understand, as “trying to make up your mind.” It’s hard to disagree with such definitions when they come wrapped in a novel that demonstrates them to be true.

The penultimate paragraph of a book review is often reserved for mild criticisms that allow the reviewer to seem objective before springing into a full-throated endorsement of the book in the final paragraph. So it is with this review. In Waldman’s novel everyone is Anglo or Jewish, or else their race is unspecified but their attributes—the name Kristen, for example—suggest they’re white. Everyone except Eugene Wu. One of the only characters with a last name, Eugene’s non-whiteness hangs around him like a weight. The novel depicts him as a striving, ill-mannered troll who exists “in a permanent state of aggrievedness. He felt it was his duty to nip at the happiness of those more fortunate.” Ouch. No wonder Eugene feels aggrieved. Making him the only racialized character in the novel feels like a lapse in Waldman’s judgment.

In any case, The Love Affairs of Nathaniel P. is a daring book, a finely wrought romance that doubles as a treatise on romance today. If a sheaf of blank pages had rough, drunken sex with n+1 magazine, it would go home imprinted with a story like this.